AU2003202805B2 - Water-soluble phthalocyanine compound-containing ink for ink jetting, ink jet recording method and method for improving ozone gas discoloration of colored image material - Google Patents
Water-soluble phthalocyanine compound-containing ink for ink jetting, ink jet recording method and method for improving ozone gas discoloration of colored image material Download PDFInfo
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- AU2003202805B2 AU2003202805B2 AU2003202805A AU2003202805A AU2003202805B2 AU 2003202805 B2 AU2003202805 B2 AU 2003202805B2 AU 2003202805 A AU2003202805 A AU 2003202805A AU 2003202805 A AU2003202805 A AU 2003202805A AU 2003202805 B2 AU2003202805 B2 AU 2003202805B2
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- ink
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- -1 phthalocyanine compound Chemical class 0.000 title claims abstract description 245
- 238000000034 method Methods 0.000 title claims abstract description 45
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000000463 material Substances 0.000 title claims description 45
- 238000007641 inkjet printing Methods 0.000 title claims description 37
- 238000002845 discoloration Methods 0.000 title claims description 14
- 238000010521 absorption reaction Methods 0.000 claims abstract description 49
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910001416 lithium ion Inorganic materials 0.000 claims abstract description 35
- 238000002835 absorbance Methods 0.000 claims abstract description 30
- 230000003595 spectral effect Effects 0.000 claims abstract description 23
- 150000002500 ions Chemical class 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims description 160
- 125000000623 heterocyclic group Chemical group 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 46
- 239000007789 gas Substances 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000003368 amide group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 11
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
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- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 10
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 10
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- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
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- 239000011701 zinc Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
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- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 7
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- 238000003384 imaging method Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229940031958 magnesium carbonate hydroxide Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- SQZZGEUJERGRIN-UHFFFAOYSA-N manganese;pentane-2,4-dione Chemical compound [Mn].CC(=O)CC(C)=O SQZZGEUJERGRIN-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000001006 nitroso dye Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical compound N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- QEIQICVPDMCDHG-UHFFFAOYSA-N pyrrolo[2,3-d]triazole Chemical compound N1=NC2=CC=NC2=N1 QEIQICVPDMCDHG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229940079839 sodium dehydroacetate Drugs 0.000 description 1
- 235000019259 sodium dehydroacetate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- FRTIVUOKBXDGPD-UHFFFAOYSA-M sodium;3-sulfanylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCS FRTIVUOKBXDGPD-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/065—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having -COOH or -SO3H radicals or derivatives thereof, directly linked to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B47/26—Amide radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/0918—Phthalocyanine dyes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002012864A JP4190187B2 (ja) | 2002-01-22 | 2002-01-22 | 水溶性フタロシアニン化合物を含むインク、インクジェット用インク、インクジェット記録方法、及び着色画像材料のオゾンガス褪色改良方法 |
| JP2002-12864 | 2002-01-22 | ||
| PCT/JP2003/000371 WO2003062323A1 (en) | 2002-01-22 | 2003-01-17 | Water-soluble phthalocyanine compound-containing ink for ink jetting, ink jet recording method and method for improving ozone gas discoloration of colored image material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003202805A1 AU2003202805A1 (en) | 2003-09-18 |
| AU2003202805B2 true AU2003202805B2 (en) | 2008-05-22 |
Family
ID=27606056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003202805A Ceased AU2003202805B2 (en) | 2002-01-22 | 2003-01-17 | Water-soluble phthalocyanine compound-containing ink for ink jetting, ink jet recording method and method for improving ozone gas discoloration of colored image material |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7219988B2 (https=) |
| EP (1) | EP1468050B1 (https=) |
| JP (1) | JP4190187B2 (https=) |
| KR (1) | KR100845446B1 (https=) |
| CN (1) | CN100379740C (https=) |
| AT (1) | ATE323743T1 (https=) |
| AU (1) | AU2003202805B2 (https=) |
| CA (1) | CA2473962C (https=) |
| DE (1) | DE60304675T2 (https=) |
| WO (1) | WO2003062323A1 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002060994A1 (en) * | 2001-01-31 | 2002-08-08 | Fuji Photo Film Co., Ltd. | Phthalocyanine compound, ink, ink for ink-jet recording, ink-jet recording method and method for improving ozone gas resistance of colored imaging material |
| TWI299744B (en) * | 2001-06-22 | 2008-08-11 | Fuji Corp | Phthalocyanine compound, ink, ink for ink-jet recording, ink-jet recording method and method for improving resistance of color-imaging material to ozone gas |
| JP2003292847A (ja) * | 2002-04-03 | 2003-10-15 | Fuji Photo Film Co Ltd | インクジェット記録用インクおよびインクジェット記録方法 |
| JP4116890B2 (ja) * | 2003-01-31 | 2008-07-09 | 富士フイルム株式会社 | インクジェット記録用インクおよび画像形成方法 |
| JP2004231863A (ja) * | 2003-01-31 | 2004-08-19 | Fuji Photo Film Co Ltd | インクジェット記録用インクおよび画像形成方法 |
| GB0316856D0 (en) * | 2003-07-18 | 2003-08-20 | Avecia Ltd | Inks and processes |
| GB2418670B (en) * | 2003-07-18 | 2007-06-27 | Avecia Inkjet Ltd | Phthalocyanines and their use in ink-jet printers |
| BRPI0412764A (pt) * | 2003-07-18 | 2006-09-26 | Avecia Inkjet Ltd | composição, mistura de corantes, processo para formar uma imagem sobre um substrato, material, e, cartucho de impressora por jato de tinta |
| MXPA06000671A (es) * | 2003-07-18 | 2006-03-30 | Avecia Inkjet Ltd | Ftalocianinas y su uso en impresoras de inyeccion de tinta. |
| JP4691318B2 (ja) * | 2003-09-01 | 2011-06-01 | 富士フイルム株式会社 | 水溶性フタロシアニン化合物の製造方法及びその合成中間体 |
| WO2005033110A1 (en) * | 2003-10-07 | 2005-04-14 | York University | Processes for producing polysubstituted phythalocyanines |
| JP4303560B2 (ja) | 2003-10-31 | 2009-07-29 | 富士フイルム株式会社 | 染料含有硬化性組成物、並びに、カラーフィルターおよびその製造方法 |
| WO2005066289A1 (en) * | 2004-01-08 | 2005-07-21 | Fuji Photo Film Co., Ltd. | Recording method |
| US7276111B2 (en) * | 2004-02-09 | 2007-10-02 | Seiko Epson Corporation | Ink composition, inkjet recording method and recorded matter |
| GB0425015D0 (en) * | 2004-11-11 | 2004-12-15 | Avecia Ltd | Phthalocyanine compounds |
| GB0427199D0 (en) * | 2004-12-11 | 2005-01-12 | Avecia Ltd | Phthalocyanines and their use in ink-jet printers |
| JP4590255B2 (ja) * | 2004-12-22 | 2010-12-01 | キヤノン株式会社 | 評価装置及び評価方法 |
| US7279034B2 (en) | 2005-03-11 | 2007-10-09 | Seiko Epson Corporation | Ink composition, ink cartridge, inkjet recording method, and recorded matter |
| US7575627B2 (en) | 2005-12-02 | 2009-08-18 | Fujifilm Imaging Colorants Limited | Phthalocyanines and their use in ink-jet printing |
| GB0524639D0 (en) * | 2005-12-02 | 2006-01-11 | Avecia Inkjet Ltd | Phthalocyanines and their use in ink-jet printing |
| JP4795221B2 (ja) * | 2005-12-21 | 2011-10-19 | キヤノン株式会社 | インク、インクジェット記録方法、記録ユニット、インクカートリッジ、及びインクジェット記録装置 |
| JP5247836B2 (ja) * | 2005-12-21 | 2013-07-24 | キヤノン株式会社 | インク、インクジェット記録方法、記録ユニット、インクカートリッジ、及びインクジェット記録装置 |
| JP2007196396A (ja) * | 2006-01-23 | 2007-08-09 | Fujifilm Corp | インクジェット記録方法及びインクジェット記録物 |
| JP2010506962A (ja) * | 2006-10-16 | 2010-03-04 | シルバーブルック リサーチ ピーティワイ リミテッド | オフセットインク中での使用に適したフタロシアニン染料 |
| GB0704970D0 (en) * | 2007-03-15 | 2007-04-25 | Fujifilm Imaging Colorants Ltd | Phthalocyanines and their use in ink jet printing |
| JP2009132891A (ja) * | 2007-10-31 | 2009-06-18 | Fujifilm Corp | インクセット、インクジェット記録方法、及び記録物 |
| JP5554025B2 (ja) * | 2008-07-10 | 2014-07-23 | 富士フイルム株式会社 | インクジェット記録方法 |
| JP2010030196A (ja) | 2008-07-30 | 2010-02-12 | Fujifilm Corp | インクジェット記録方法 |
| JP2010030197A (ja) | 2008-07-30 | 2010-02-12 | Fujifilm Corp | インクジェット記録方法 |
| JP2010077285A (ja) | 2008-09-26 | 2010-04-08 | Fujifilm Corp | インクセット及び画像形成方法 |
| CN102216397A (zh) * | 2008-10-30 | 2011-10-12 | 惠普开发有限公司 | 具有扩展共轭的酞菁染料、使用它的油墨和检测系统 |
| CN102482505A (zh) * | 2009-07-31 | 2012-05-30 | 惠普开发有限公司 | 用于喷墨油墨的近红外吸收酞菁和萘酞菁 |
| GB0917533D0 (en) | 2009-10-07 | 2009-11-25 | Fujifilm Imaging Colorants Ltd | Azaphthalocyanines and their use in printing |
| GB201004416D0 (en) * | 2010-03-17 | 2010-05-05 | Fujifilm Imaging Colorants Ltd | Phthalocyanines and their use in ink-jet printing |
| CN102558947A (zh) | 2010-12-10 | 2012-07-11 | 精工爱普生株式会社 | 油墨组合物、使用其的记录方法以及记录物 |
| CN102558948B (zh) | 2010-12-10 | 2016-02-10 | 精工爱普生株式会社 | 油墨组合物、使用其的喷墨记录方法以及记录物 |
| WO2013120273A1 (zh) * | 2012-02-17 | 2013-08-22 | 大连理工大学 | 铜酞菁苄砜基化合物及其衍生物 |
| CN103289435B (zh) * | 2013-03-04 | 2015-09-02 | 连云港市添立润化工有限公司 | 一种液晶显示屏用颜料衍生物及其制造方法 |
| US10058542B1 (en) | 2014-09-12 | 2018-08-28 | Thioredoxin Systems Ab | Composition comprising selenazol or thiazolone derivatives and silver and method of treatment therewith |
| CN105504994B (zh) | 2014-10-14 | 2022-09-06 | 海德堡印刷机械股份公司 | 喷墨打印用的水基近红外干燥墨水 |
| JP6705184B2 (ja) | 2016-01-28 | 2020-06-03 | セイコーエプソン株式会社 | インクジェット捺染用浸透液、インクジェット捺染方法及びインクジェット捺染装置 |
| EP4019255A4 (en) * | 2019-08-23 | 2022-10-12 | FUJIFILM Corporation | DYE INK COMPOSITION, CYAN DYE INK, DYE INK FOR INKJET PRINTING, INKJET PRINTING PROCESSES AND AQUEOUS DYE SOLUTION |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07138511A (ja) * | 1993-11-18 | 1995-05-30 | Ricoh Co Ltd | インクジェット記録用インク |
| JP3744981B2 (ja) * | 1995-09-14 | 2006-02-15 | オリヱント化学工業株式会社 | 新規フタロシアニン又はナフタロシアニン誘導体 |
| DE19634354A1 (de) * | 1996-08-26 | 1998-03-05 | Clariant Gmbh | Wasserlösliche Kupferphtalocyanin-Farbstoffe, ihre Herstellung und Verwendung |
| US6569212B2 (en) * | 1997-04-26 | 2003-05-27 | Avecia Limited | Phthalocyanine ink-jet dyes |
| JP2001011076A (ja) * | 1999-04-27 | 2001-01-16 | Nippon Kayaku Co Ltd | フタロシアニン化合物、水性インク組成物及び着色体 |
| CN1348456A (zh) | 1999-04-27 | 2002-05-08 | 日本化药株式会社 | 酞菁化合物,水基墨水组合物和彩色制品 |
| GB2341868A (en) | 1999-11-26 | 2000-03-29 | Avecia Ltd | Sulpho and phenylaminosulphonyl substituted phthalocyanine derivatives and their use in ink jet inks |
| GB0005299D0 (en) * | 2000-03-07 | 2000-04-26 | Avecia Ltd | Compound, compositions and use |
| GB0005301D0 (en) * | 2000-03-07 | 2000-04-26 | Avecia Ltd | Compound, composition and use |
| TWI290946B (en) | 2000-07-26 | 2007-12-11 | Nippon Kayaku Kk | Cyan dye mixture, aqueous cyanic ink composition and ink-jet printing method |
| WO2002060994A1 (en) * | 2001-01-31 | 2002-08-08 | Fuji Photo Film Co., Ltd. | Phthalocyanine compound, ink, ink for ink-jet recording, ink-jet recording method and method for improving ozone gas resistance of colored imaging material |
| WO2002088256A1 (en) | 2001-04-27 | 2002-11-07 | Daiwa Dyestuff Mfg. Co., Ltd. | Oxidation-resistant water-soluble dye of copper/phthalocyanine compound complex, dye composition containing the same, and recording fluid |
-
2002
- 2002-01-22 JP JP2002012864A patent/JP4190187B2/ja not_active Expired - Fee Related
-
2003
- 2003-01-17 DE DE2003604675 patent/DE60304675T2/de not_active Expired - Lifetime
- 2003-01-17 CA CA 2473962 patent/CA2473962C/en not_active Expired - Fee Related
- 2003-01-17 US US10/502,217 patent/US7219988B2/en not_active Expired - Lifetime
- 2003-01-17 WO PCT/JP2003/000371 patent/WO2003062323A1/en not_active Ceased
- 2003-01-17 CN CNB03802568XA patent/CN100379740C/zh not_active Expired - Lifetime
- 2003-01-17 KR KR20047011281A patent/KR100845446B1/ko not_active Expired - Fee Related
- 2003-01-17 AT AT03701768T patent/ATE323743T1/de not_active IP Right Cessation
- 2003-01-17 AU AU2003202805A patent/AU2003202805B2/en not_active Ceased
- 2003-01-17 EP EP20030701768 patent/EP1468050B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4190187B2 (ja) | 2008-12-03 |
| CN1653138A (zh) | 2005-08-10 |
| CN100379740C (zh) | 2008-04-09 |
| KR100845446B1 (ko) | 2008-07-10 |
| JP2003213167A (ja) | 2003-07-30 |
| ATE323743T1 (de) | 2006-05-15 |
| WO2003062323A1 (en) | 2003-07-31 |
| US7219988B2 (en) | 2007-05-22 |
| EP1468050A1 (en) | 2004-10-20 |
| DE60304675T2 (de) | 2006-08-31 |
| KR20040075946A (ko) | 2004-08-30 |
| CA2473962A1 (en) | 2003-07-31 |
| EP1468050B1 (en) | 2006-04-19 |
| DE60304675D1 (de) | 2006-05-24 |
| CA2473962C (en) | 2009-09-29 |
| US20050073563A1 (en) | 2005-04-07 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |